Triethylamine → HCID 11998535, compound

HRID 2102720Notes

Reaction equation

HRID 2102720 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)([CH:12]3[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[N:33]1([C:39](=[O:50])[CH2:40][N:41]2[CH2:46][CH2:45][N:44]([C:47](Cl)=[O:48])[CH2:43][CH2:42]2)[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)([CH:12]3[CH2:17][CH2:16][CH2:15][N:14]([C:47]([N:44]4[CH2:43][CH2:42][N:41]([CH2:40][C:39]([N:33]5[CH2:34][CH2:35][O:36][CH2:37][CH2:38]5)=[O:50])[CH2:46][CH2:45]4)=[O:48])[CH2:13]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 15700340HCID 15700340, compoundHCID 57803070Rac-6-chloro-3-(3-chloro-benzyl)-3-piperidin-3-yl-1,3-dihydro-indol-2-one

Product 1

HCID 11998535HCID 11998535, compound

Procedure

To a solution of rac-6-chloro-3-(3-chloro-benzyl)-3-piperidin-3-yl-1,3-dihydro-indol-2-one (90 mg, 0.24 mmol) (from Example 25a supra) in tetrahydrofuron (3 mL) was added triethyl amine (60 mg, 0.60 mmol) (Aldrich), followed by the addition of 4-(2-morpholin-4-yl-2-oxo-ethyl)-piperazine-1-carbonyl chloride (99 mg, 0.36 mmol) (from Example 48a supra). The mixture was stirred at room temperature for 30 minutes. The mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water, brine, dried over Na2SO4 and concentrated. The residue was purified by chromatography to give rac-6-chloro-3-(3-chloro-benzyl)-3-{1-[4-(2-morpholin-4-yl-2-oxo-ethyl)-piperazine-1-carbonyl]-piperidine-3-yl}-1,3-dihydro-indol-2-one as a white solid. (Yield 70 mg, 47.6%).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-fd9c18db042c4da4996011efbe3bbc22
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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